Sodium Hydroxide → 3-Bromo-6,7-dihydro-5H-cyclopenta(b)pyridine

To a solution of 6,7-dihydro-5H-[1]pyrindine (20 gm) and AlCl3 (56 gm) at 100° C. was added 10 mL of bromine over 2 hours, stirred an additional 15 minutes, cooled to room temperature, and poured over ice. The pH of the reaction was adjusted until it was basic with NaOH and then celite and ether were added and the mixture filtered. The filter cake was washed well with additional ether and the filtrate was extracted from the aqueous layer. The ether layer was washed with saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated to dryness. The residue was chromatographed on silica gel using 10:1 hexane/ethyl acetate as the eluant to yield 4 gm of compound. 1H NMR (CDCl3): d 8.35 (s, 1 H), 7.60 (s, 1 H), 2.90 (m, 4 H), 2.10 (m, 2 H).

1. additionpoured over ice
2. filtrationthe mixture filtered
3. washThe filter cake was washed well with additional ether
4. extractionthe filtrate was extracted from the aqueous layer
5. washThe ether layer was washed with saturated aqueous NaCl solution
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated to dryness
9. customThe residue was chromatographed on silica gel using 10:1 hexane/ethyl acetate as the eluant

ORDレコード

ord-538f16fac4a14554845341b535fa28eb

出典データセット

uspto-grants-1994_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05338740